Ester from chaulmoogra-oil.



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LUDWIG TAUB, OLE ELBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORM. FRIEDR. BAYER & 00., OF ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

ESTER FROM CHAULMOOGRA-OIL.

No Drawing. Application filed February 9, 1309.

Specification of Letters Patent.

Serial No. 476,980. (Specimens) .many, have invented new and useful Im provements in Esters from Ohaulmoogra- Oil, of which the following is a specification.

As is known chaulmoogra-oil (obtained from the seeds of Tamktogenos Kurez'z') is largely used in the treatment of leprosy and variousskin diseases. This oil however, has. the disadvantage for its use in medicine, that it is of a butter like consistency which renders it useless for subcutaneous injection and that it shows acid reaction. Furthermore it has a very tenacious disagreeable odor and an unpleasant taste.

I have now found that neutral valuable therapeutic products can be obtained from chaulmoogra-oil in the following way: The chaulmoogra-oil is saponified by a suitable treatment with alkalies or steam and subsequently transformed into the free acids.

The mixture of acids thus obtained. is then freed from the malodorous by-products by treatment with steam or by washing with hot water and is then converted into esters by' esterification in the usual way 6. g; by treatment with methylethylor propylalcohol and sulfuric acid. By distillation in oaouo pure neutral almost odorless,

tasteless and colorless limpid' oils are obtained which can also be used for subcutaneous injections. The new preparations have proved to be very valuable remedies against leprosy, an average dose being from 1 to 3 grams. They are insoluble in water and soluble in ether and alcohol.

The new esters can be saponified in the usual'way and the free fatty acids precipitated by means of sulfuric acid. If the mixture of free fatty acids is then subjected to fractional crystallization from alcohol,

chaulmoogric acid can -be isolated there from. This acid has been described by Power'and Gornall (Journal of the Chemz'cal Society, 85 I. 1904, p. '846.) It has the. formula (3 E 0 and melts at 68? O.

In carrying -outmy new process practically I can proceed as follows, the parts being by weight Example: One part of chaulmoogra-oil is saponified by heating it with a 10 percent.

alcoholic caustic potash lyef The resulting soap is dissolved in water, the'solution is acidulated with dilute hydrochloric acid and the precipitate is washed with hot Water or treated with steam until the disagreeable odor has disappeared. For the preparation of the mixture of ethyl esters the well dried mixture of acids is heated on the water Patented May 10', who.

bath for about 12 hours with three times its quantity of ethyl alcohol and a small quan-- tity of a mineral acid. The mixture of esters thus obtained is shaken with a solution of sodium carbonate and then with water until it is completely neutral and it is then distilled under reduced pressure. It passes over at from 190220 O. at a pressure of 15 mm. as a colorless, almost oderless and tasteless limpid oil of neutral reaction. It is practically insoluble in water and soluble in alcohol and ether.

The process is carried out in an analogous way for the preparation of other alkyl esters e. g. the methyl and the propyl esters. Other purification may be used.

Having now described my invention and in what manner the same is to'be performed,

what I claim as new, and desire to secure by -'Letters Patent is 1. The herein-described process of produoing esters from chaulmo'ogra-oil, which process consists in first saponifying chaul- 'moogra-oil, secondly acidulating and =ur1- fyin the mixture of acids thus obtained,

thirdly esterifying the mixture of acids thus purifiedand finally distilling the-esters in. vacuo. 2. The herein-described process of producing a preparation from chaulmoogra-oil,

which process consists'in first saponifying chaulmoogra-oil, secondly acidulating 'and purifying the mixture of acids thus obtained, thirdly esterifying the mixture'ofacids thus purified with ethyl alcohol to obtain the mixture of ethyl esters and finally distilling these ethyl esters in oacuo.

3. The herein-described mixture of almost odorless and tasteless esters from chaulmoogra -oil, which is a limpid neutral oil, soluble in-ether and in alcohol, insolublev in water,

yielding on saponific-ation a mixture cont-ainmg fatty acids from which chaulmoogric acid of the formula O H O and the melting point of.68 C. may be isolated; and ex- .hibiting valuable therapeutic properties.

4. The. herein-described almost odorless and tastele'ss mixture of ethylesters obtain-$ able from chaulmoogra-oil, which is a "'"nhand lzhe presence of two subsc rib ing pid' neutral colorless oil; boiling at 190 to witlieeees.

220 C. under a pressure of about 15 mm." r I I I l soluble in alcohol and ether, and insoluble: U W U 5 in Water; and exhibiting valuable therapeu- Witnesses:

tic properties. O'i'ro KiiNIG,

In testimony whereof I have hereunto set I W. W. BoUNsWIETz. 

